Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction andδ-lactam formation:remote enantioselecitvity control and dynamic kinetic asymmetric transformation  

作　　者：Jie Lv Jun Xu Xuling Pan Zhichao Jin Yonggui Robin Chi 

机构地区：[1]State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Guizhou University,Guiyang 550025,China [2]School of Pharmacy,Guizhou University of Traditional Chinese Medicine,Guiyang 550025,China [3]Division of Chemistry&Biological Chemistry,School of Physical&Mathematical Sciences,Nanyang Technological University,Singapore 637371,Singapore

出　　处：《Science China Chemistry》2021年第6期985-990,共6页中国科学（化学英文版）

基　　金：This work was supported by the National Natural Science Foundation of China(21772029,21801051,21961006,22071036,82360589,81360589);The 10 Talent Plan(Shicengci)of Guizhou Province([2016]5649);the Guizhou Province Returned Oversea Student Science and Technology Activity Program[(2014)-2];the Science and Technology Department of Guizhou Province([2018]2802,[2019]1020);the Program of Introducing Talents of Discipline to Universities of China(111 Program,D20023);at Guizhou University,Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules,Department of Education,Guizhou Province[Qianjiaohe KY(2020)004];the Guizhou Province First-Class Disciplines Project[(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008];Guizhou University of Traditional Chinese Medicine(China),and Guizhou University.

摘　　要：An N-heterocyclic carbene(NHC)-catalyzed enantioselective Mannich reaction of the remoteγ-carbon of cyclopropylcarbaldehydes is disclosed for the first time.Diastereo-and enantiomerically enriched multicyclicδ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation(DYKAT)processes.Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities.

关 键 词：N-heterocyclic carbene ORGANOCATALYSIS dynamic kinetic asymmetric transformation 1-cyclopropylcarbaldehydes asymmetric reactions 

分 类 号：O621.251[理学—有机化学]